Skip to main content
placeholder image

Studies in the cycloproparene series: Halogenation and dehydrohalogenation of some 1a, 9b-dihydrocyclopropa[l]phenanthrenes

Journal Article


Abstract


  • Dehydrohalogenation of (1α, 1aβ, 9aβ)-1-chloro-1a, 9b-dihydrocyclopropa[l]phenanthrene (4b) yields products by way of the corresponding dibenzobicyclohepta-2, 4, 6-triene (5b) whilst under solvolytic conditions the 7-t-butoxydibenzocyclohepta-1, 3, 5-triene (11b) is formed by cyclopropyl-allyl ring expansion. When subjected to bromination the cyclopropaphenanthrenes (4a, c) yield halophenanthrenes (14a) and (15c) by cleavage of an external bond of the cyclopropane ring. © 1983, CSIRO. All rights reserved.

Publication Date


  • 1983

Citation


  • Studies in the cycloproparene series: Halogenation and dehydrohalogenation of some 1a, 9b-dihydrocyclopropa[l]phenanthrenes (1983). Australian Journal of Chemistry, 36(6), 1167-1175. doi:10.1071/CH9831167

Scopus Eid


  • 2-s2.0-84970583203

Start Page


  • 1167

End Page


  • 1175

Volume


  • 36

Issue


  • 6

Abstract


  • Dehydrohalogenation of (1α, 1aβ, 9aβ)-1-chloro-1a, 9b-dihydrocyclopropa[l]phenanthrene (4b) yields products by way of the corresponding dibenzobicyclohepta-2, 4, 6-triene (5b) whilst under solvolytic conditions the 7-t-butoxydibenzocyclohepta-1, 3, 5-triene (11b) is formed by cyclopropyl-allyl ring expansion. When subjected to bromination the cyclopropaphenanthrenes (4a, c) yield halophenanthrenes (14a) and (15c) by cleavage of an external bond of the cyclopropane ring. © 1983, CSIRO. All rights reserved.

Publication Date


  • 1983

Citation


  • Studies in the cycloproparene series: Halogenation and dehydrohalogenation of some 1a, 9b-dihydrocyclopropa[l]phenanthrenes (1983). Australian Journal of Chemistry, 36(6), 1167-1175. doi:10.1071/CH9831167

Scopus Eid


  • 2-s2.0-84970583203

Start Page


  • 1167

End Page


  • 1175

Volume


  • 36

Issue


  • 6